Chemoselective Trifluoroethylation Reactions of Quinazolinones and Identification of Photostability

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Title
Chemoselective Trifluoroethylation Reactions of Quinazolinones and Identification of Photostability
Author(s)
Saikat Maiti; Jaeshin Kim; Jae-Heon Park; Dongsik Nam; Jae Bin Lee; Ye-Jin Kim; Jung-Min Kee; Jeong Kon Seo; Kyung Jae Myung; Jan-Uwe Rohde; Wonyoung Choe; Oh-Hoon Kwon; Sung You Hong
Publication Date
2019-06
Journal
JOURNAL OF ORGANIC CHEMISTRY, v.84, no.11, pp.6737 - 6751
Publisher
AMER CHEMICAL SOC
Abstract
© 2019 American Chemical Society.Herein, we report chemoselective trifluoroethylation routes of unmasked 2-arylquinazolin-4(3H)-ones using mesityl(2,2,2-trifluoroethyl)iodonium triflate at room temperature. Homologous C-, O-, and N-functionalized subclasses are accessed in a straightforward manner with a wide substrate scope. These chemoselective branching events are driven by Pd-catalyzed ortho-selective C-H activation at the pendant aryl ring and base-promoted reactivity modulation of the amide group, leveraging the intrinsic directing capability and competing pronucleophilicity of the quinazolin-4(3H)-one framework. Furthermore, outstanding photostability of the quinazolin-4(3H)-one family associated with nonradiative decay is presented
URI
https://pr.ibs.re.kr/handle/8788114/6151
ISSN
0022-3263
Appears in Collections:
Center for Genomic Integrity(유전체 항상성 연구단) > Journal Papers (저널논문)
Center for Soft and Living Matter(첨단연성물질 연구단) > Journal Papers (저널논문)
Files in This Item:
2019_Kwon_J.Org.Chem._Chemoselective Trifluoroethylation Reactions of Quinazolinones and Identification of Photostability.pdfDownload

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